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Synthesis of gem-Difluorinated 1,3-Dienes via Synergistic Cu/Pd-Catalyzed Borodifluorovinylation of Alkynes.

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gem-Difluoroalkenes (=CF2), which normally act as metabolically stable bioisosteres for carbonyl groups (C═O), are widely applied in agrochemicals and pharmaceuticals and are also used as building blocks in organic synthesis.… Click to show full abstract

gem-Difluoroalkenes (=CF2), which normally act as metabolically stable bioisosteres for carbonyl groups (C═O), are widely applied in agrochemicals and pharmaceuticals and are also used as building blocks in organic synthesis. Herein, an example of Cu/Pd-catalyzed borodifluorovinylation was achieved using alkynes, difluoroethylene bromide, and B2pin2 as chemical feedstocks, providing the corresponding conjugated gem-difluoroalkene scaffold with good functional group compatibility. Moreover, an array of fluorinated synthons can be obtained through further transformations.

Keywords: gem difluorinated; gem; catalyzed borodifluorovinylation; difluorinated dienes; synthesis gem

Journal Title: Organic letters
Year Published: 2022

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